


Crossing Dean

by Evil_Knitter (Nichneven13)



Series: -Ing Dean Series [2]
Category: Supernatural
Genre: Crack, Drag Queens, Gen, M/M, cross-dressing
Language: English
Status: Completed
Published: 2010-09-22
Updated: 2010-09-22
Packaged: 2018-02-26 12:55:20
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,967
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2652752
Author URL: https://archiveofourown.org/users/Nichneven13/pseuds/Evil_Knitter
Summary: <blockquote class="userstuff">
              <p>Flat broke and desperate, the boys turn to a life of drag for extra cash.</p>
            </blockquote>





	Crossing Dean

**Author's Note:**

> Second in the -Ing Dean series. Officially Dean/Cas from here on out. Originally posted to LiveJournal.

There is a little joint at the corner of Church and Granby in Norfolk, Virginia called Nutty Buddies. The third Thursday of every month is amateur night, with a five hundred dollar prize to the winner. It was the easiest cash in town, as far as Dean was concerned. Norfolk, it was proving, was not a town big on pool or darts. What it was big on… was drag queens, which made sense because of the military base.

"I'm pretty as hell," Dean hollered at his laughing brother. "Are you saying I'm not hot enough to win?"

"Dude," Sam wiped his eyes and made a placating gesture. "I'm not qualified to judge your relative hotness. I'm just saying that the thought of you as a drag queen is hilarious."

"I think you're hot enough to win," Cas remarked from the bed he shared with Dean. He idly flipped through the latest issue of _Angel News Weekly_.

"Thanks, Cas," Dean raised his fist in victory and smirked at Sam.

"Okay," Sam said with a sigh. No way was he getting into a debate over his brother's looks. "Even if I concede the point of your hotness—which I'm not—how do you plan to do it? I mean, it's not like you have, um, spare panty hose and hooker shoes in your duffel. I mean… do you?"

Cas looked up from an article on the renovations on St. Peter's Gate, extremely interested in Dean's reply.

"Of course not," Dean said. "But a quick stop at Nancy's Nook and I should be good to go."

Sam bit his lower lip and tried to find an argument he could use to talk Dean out of his cockamamie plan. He could point to the gayness of the venture, but that was a given, and honestly, Dean had been embracing more and more of his inner gay since he first slipped the pickle to Cas. Which, you know, made sense.

"Dude," Sam's eyes lit up as he hit upon a key point that just might do the trick. "You know you'll have to tuck your junk, right?"

Dean stared at his brother, confused. Cas closed his magazine and sat up, completely invested in the conversation now. He knew Dean inside and out; he could anticipate nearly every move before the man had ever settled on a course of action. But this one—talk of tucking his _junk_ —he couldn't even guess at the coming response.

"Um…" Dean said and shifted his stance. Okay, so that was close to what Cas would've guessed.

"Yeah," Sam said, already planning his triumph. "You have to push your testicles back into your abdomen. And tape. There's tape."

"Dude…" Cas said from the bed, which was weird for him. He typically refrained from using the catchall word because he was typically armed with appropriate words to express himself. This time, not so much.

"How do you know how to tuck?" Dean asked when it became apparent Cas could not get the question out. "I mean, _dude_."

"Shut up," Sam grumbled, his cheeks exploding with the color of summer strawberries. "The point is, you can't just throw on a muu-muu and hope your pretty face gets you by. Being a drag queen is about attitude and showmanship."

"Again, I ask: how do you know this stuff?"

"Again, I say: shut up."

"What song will you perform?" Cas asked suddenly, bringing two sets of Winchester eyes to him in a hurry.

"Yeah, Dean," Sam grinned, and suddenly, he was very much on board with the plan to get Dean tarted up and on stage at Nutty Buddies. "A little Whitney? Maybe Mariah? You should break out that drag spin you wanted to do in the Dance Off."

"Diana Ross!" Cas suggested.

"Ooooh," Sam snapped is fingers in grand revelation. "Diana Ross, FTW!"

"We better get to Nancy's," Dean said with a roll of the eyes. He didn't know why Sam liked to pretend he was straight when he was clearly the biggest fairy in gay creation. Diana Ross… really? "Do we have any of that cloth tape in the first aid kit? I don't want to lose any skin."

 

****

 

"I vote for the blue one," Sam said, picking a bejeweled and bebeaded barely-there dress out of the pile of discards. "You look good in blue."

Dean shot his brother a disturbed look.

"I would normally agree," Cas said because Dean did look smokin' hot in blue. He held up a soft pink dress with marabou feathers along the hem. "But I think pink is the way to go. Your skin tone just begs for pink. Plus, the cap sleeves will make your shoulders look smaller."

"I don't do pink," Dean said with a scowl.

"Yeah, well, you don't do sequins and jewels either," Cas pointed out with a patient blink. Or it could've been a blink of Well Duh. "Man up and wear the pink."

The things Dean did for his boyfriend was beyond reason. He took the pink frock, holding it out at arm's length and crossed to the register, where a pile of supplies were stocked on the eye level counter. Why did adult novelty stores always have a high and mighty counter? Al the cashier sat high above it all, lording over the puny peasants in search of earthly desires. Hmph.

"Good choice," Al commented, taking the pink dress and folding it carefully. "You heading out to Nutty Buddies tonight?"

"Yeah."

"You tell that bitch Amanda Peon that she better come see me soon," Al said as he scanned a pair of lace up boots.

"We will relay the message," Cas said with a serious nod. "To that bitch Amanda Peon."

Al peered down at Cas, cataloging his blue eyes, full lips and lithe form. "Huh," he said at last and shrugged. "Why aren't you the one doing this?"

Sam made a strangled sound that could have been a laugh.

"Dean is prettier than I am," Cas said, smiling over at his boyfriend. "Everyone knows that."

"Says who?" Al asked with an appraising look at Dean.

Dean blew his lips out, offended. Not like _he_ didn't think Cas was the hottest thing on two legs, because he totally did. Cas naked and sweaty was The Most Awesome Sight Ever, but it was publicly accepted that Dean was hotter. He looked to Sam for validation and sympathy. He found neither.

"You know," Sam said instead, starting in on one of his Crazy Ideas. "He has a point. Cas has no inhibitions."

"I do so!" Cas objected.

"Dude," Sam rolled his eyes and really wished he didn't have to pull out an example to prove his point. "Just last week you dropped trough in a Denny's to show the waitress Jimmy's unicorn-shaped birthmark. The week before that, you sang "Walk the Dinosaur" in the middle of Wal-Mart. The week before that—"

"Touché," Cas admitted with a chuckle. Maybe his human impulse to rational thought process wasn't yet fully developed.

"Cas…" Dean groaned. "No French."

"Are you up for it?" Sam asked Cas. As much as he wanted to see Dean in drag— _gagging_ to see it actually—they needed the cash and the silly little angel was a better bet. "You could rock that pink dress way better than Mr. Shoulders over there."

"I do look good in pink," Cas said with a sigh. "Sure, sign me up."

Dean guppied at the scene before him. He had been exacto'd out of The Plan with the precision of a kidnapper cutting out letters from a newspaper. Cas, Sam and Al—how the fuck did _Al_ get a front row seat to The Plan?—discussed glitter, eye liner and proper tucking techniques. Dean crossed his arms over his chest and pouted, not that anyone gave a damn to notice.

 

****

 

"How do I look?" Cas asked the assembled cast back at the motel. He spun slowly in a circle, showing off legs that went up to There and a generous C cup. The marabou danced gently around his thighs, tickling against his tight fishnets.

Dean grunted and licked his lips because, really, his boyfriend was pretty damn hot as a tranny. But there are some things that he won't say out loud.

Sam cleared his throat and scratched at neck because, really, his brother's boyfriend was pretty damn hot as a tranny. But there are some things that he won't say out loud.

Al whistled like Cas was a chick strutting past a construction site because, really, dude looked like a hot lady.

"I need a name," Cas declared as he checked his lipstick in his hand mirror. Sam had drawn a beauty mark beside his mouth and slathered his eyelids in Tramp Stamp Silver glitter. "Did you narrow down the list of possibilities while I was tarting up?"

"Uh, yeah," Dean reached out and took the list from Al who, seriously, was still there. "We like Chi Chi La Roue, Ivanna Jackacockoff, and Zsa Zsa LaHore."

"Two of those are French," Cas pointed out, making Dean cringe and crumple the list. "What about Mama Cas?"

"Oh," Sam said with a blink and then a laugh. "That's pretty funny. I mean, to us."

 

****

 

"Welcome to Nutty Buddies' infamous Amateur Night," a huge queen with huger hair said into her bedazzled microphone. "I'm your hostess snack cake with cream filling, Hope Heelcum!"

Dean snorted into his beer at the name. He hated to admit he was relieved to be sitting in the audience rather than standing on stage under the glare of the glitter ball. Cas had four competitors, but Dean was certain they had the cash in the bag.

The first three queens took their turns, sashaying, spinning and neck-sliding as they lipped along to such classics as "I Am Woman", "Vogue" and "R-E-S-P-E-C-T". They were good, Sam and Dean… and freakin' _Al_ had to admit. In fact, Holly Mackeral's turn as Madonna in a full pointy bra and swinging pony tail had their palms sweating. If Cas didn't nail it, they'd be SOL.

The first strains of Jennifer Hudson's "And I'm Telling You I'm Not Going" fired up and garnered a few whoops of approval from the Broadway gays in the club. Dean had been nervous about the selection. There were no opportunities to execute a flawless drag queen spin; no chances to bend at the waist and shake his pert little ass.

Cas' slender wrists floated through the air as he reached out to his pretend, abandoning lover. His face contorted into the prettiest vision of heartbreak known to man. His lips—pinched to their fullest and glossed by Dean himself—quivered as they wrapped around the lyrics of the song.

"This is going to be great," Al scooted forward in his chair, his eyes as glossy as Cas' lips. "She's going to nail it."

Sam grabbed Dean's arm and stilled it where it was, raised in the air and ready to smash into Al's stupid head. "Come on, man," Sam said as he forced his brother's arm down to his side. "Check the jealousy bullshit or you're going to miss seeing this. Look."

Dean flicked his gaze to the stage, but stayed tense and ready to beat the attraction straight out of Al's entirely too intent eyeballs. The dick. Cas had crouched down, trailing his fingertips across the lip of the stage, tears balancing precariously on his lower eyelids. Those closest to Cas drew in surprised breaths and leaned forward, matching Al's position almost exactly.

Cas drew himself upright as the song took a turn to the faster side. He staggered upstage, looking away from the audience, but grabbing at the air in desperation. Dean joined the rest of the crowd in leaning forward, spellbound as Cas rolled his head back and clawed at his ample bosom. He jumped in surprise when Cas stomped his high heeled feet with the beat and slashed his arms out wide, head tilted back as if praying to his Father.

"Jesus, Cas," Dean whispered.

"Dude," Sam elbowed his brother. He gestured to the people standing up and drifting toward the stage, dollar bills extended in their hands. "Cas is a diva."

Dean's mouth twisted around to show his pride. Damn straight his angel was a diva.

On the stage, the song was amping up, giving over to the histrionic wails of Jennifer Hudson begging and pleading. Cas ran from one side of the stage to the other, bending deep to reach the dollars being offered to him in worship. His hands were stuffed with money, but for emphasis to a strong lyric, he threw it all to the ground at his feet.

He tore at the marabou on the hem of his dress and let it dangle as he camped out.

And then, on a particularly long note of warbling, he stumbled back again and in a stroke of effin' genius, reached up and snatched the long black wig off his head.

The crowd exploded, cheering, stomping, woo-ing and you-go-girl-ing. Cas held the wig aloft and spun it wide. Dean found himself on his feet, tense and ready to defend Mama Cas should the crowd decide to lay hands on her—him—whatever.

When Cas hit his knees, arms—and wig—up high, the cheering gave way to chants of "Mama, Mama, Mama!"

The music died away, but the applause was long in its death. Finally, Cas got to his feet, executed the dantiest little curtsy any of them had ever seen in their damn lives, and skipped off the stage.

"Damn," Al said, falling back into his seat. "That was hot."

"Shut your cakehole," Dean snapped.

"You better go collect the money from the stage," Sam suggested. "That looks like a cool two hundred up there."

"I'm on it," Dean bolted to the stage and bent over and over to scoop the money his man— _his man_ —had earned honestly. He tried to ignore the catcalls and whistles, but found it impossible. His face flushed and he was sure it was from more than just hanging upside down for a few seconds at a time.

"Well," Hope Heelcum took to the stage as soon as Dean had collected the last of the cash. She fanned herself pointedly. "I don't know what was hotter, Mama Cas, or her ass-ilicious little drag puppy. Woo!"

Dean melted down into his seat, willing the audience to die the death of the damned as they whirled to drag their hungry eyes over him one last time.

"I think it is safe to say Mama Cas is our winner," Hope declared. Dean gave one very uncharacteristic _woo, yeah, Cas_ before blushing and clamping his mouth shut. Hope waved Cas forward from the eaves of the stage. The audience whooped again as Mama Cas made her way back to the stage, a bemused and shy smile playing on her lips. She waved to her admirers, wig still in hand. "Mama, I hope we see you back in here next month! Wouldn't we like that, chickens?"

Another loud cheer.

Oh, Dean so didn't think so. He didn't want those vultures to sink their teeth into _his_ carrion, dammit.

It took Cas nearly half an hour to make his way through the congratulatory crowd. Sam kept Dean firmly against his side with an iron arm. Together, they watched Cas accept shot after shot—and number after number—from his fans. When Al draped an overly familiar arm over Cas' shoulders, Dean snapped.

"That's _it_ ," Dean slammed his beer onto the sticky bar, yanked free of Sam's grip and stalked across the room to his boyfriend. "Cas," he growled. "We're leaving."

"I won, Dean," Cas grinned down at him. He was a cool two inches taller than Dean in his heels. That was pretty awesome—to Cas anyway. "They love me!"

"Damn straight I do," Al said with a sigh. He gazed at Cas with sickening adoration. "I'll steal her away from you, dude, watch out."

"That's seriously it," Dean yelled and pounced on Al like howler monkey on a tree. Al gave a satisfyingly girly scream and hit the floor. "Cas is a _man_! Cas is _my_ man!"

Cas and Sam shared the burden of stripping Dean away from their drag queen advisor. They pulled him from smoky bar, ignoring his outraged bellows and threats to rip various organs directly out of Al's body.

It was a tense drive back to the Shadow Shack Motor Court. Cas sat in the backseat next to his still seething boyfriend. He leaned his head against Dean's shoulder, glitter snowing down from his face. Sam kept his peace, and wisely cranked up the soothing sounds of Metallica.

"They wanted to eat you alive," Dean said for the eighth time, squeezing Cas' hand for emphasis. "What a stupid idea, Sam."

Sam opened his mouth to remind his jerkass brother that the drag queen thing had, indeed, been _Dean's_ idea, but the green fire trying to burn through the rearview mirror convinced him that sometimes blame was a tastier dish than a knuckle sandwich.

"Not even worth the five hundred," Cas agreed, shooting Sam an apologetic glance.

"Actually, it's seven hundred," Sam said, figuring that was safe enough.

"Hm," Cas' brow scrunched up, dropping more glitter on Dean's shoulder.

"Don't even think about it," Dean said tersely. "As soon as we get back to the motel, we're throwing all this crap away."

Cas acquiesced easily. He wanted Dean happy, more so than he needed seven hundred dollars and an adoring flock of fans.

"Well," Dean amended, tilting his head to whisper into Cas' ear. "We'll keep the glitter. And the shoes."

Sam kept his eyes straight ahead and pretended he hadn't heard that.

Cas grinned.

~~END~~


End file.
